HU225153B1 - Crystal modifications of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide, their use and pharmaceutical compositions containing them - Google Patents
Crystal modifications of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide, their use and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU225153B1 HU225153B1 HU0002113A HUP0002113A HU225153B1 HU 225153 B1 HU225153 B1 HU 225153B1 HU 0002113 A HU0002113 A HU 0002113A HU P0002113 A HUP0002113 A HU P0002113A HU 225153 B1 HU225153 B1 HU 225153B1
- Authority
- HU
- Hungary
- Prior art keywords
- weak
- medium
- strong
- difluorobenzyl
- triazole
- Prior art date
Links
- 238000012986 modification Methods 0.000 title claims description 52
- 230000004048 modification Effects 0.000 title claims description 52
- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 title claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 239000013078 crystal Substances 0.000 title description 8
- 238000001228 spectrum Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 238000001757 thermogravimetry curve Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000005079 FT-Raman Methods 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 238000001028 reflection method Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 5
- -1 1- (2,6-difluorobenzyl) -1H-1,2,3-triazole-4-carboxamide compound Chemical class 0.000 claims 3
- 101100186386 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nak1 gene Proteins 0.000 claims 1
- 238000002835 absorbance Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000003826 tablet Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000001237 Raman spectrum Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JSZUBPHMRHROHZ-UHFFFAOYSA-N 2-(azidomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CN=[N+]=[N-] JSZUBPHMRHROHZ-UHFFFAOYSA-N 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 239000004353 Polyethylene glycol 8000 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 238000004279 X-ray Guinier Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940085678 polyethylene glycol 8000 Drugs 0.000 description 1
- 235000019446 polyethylene glycol 8000 Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH140497 | 1997-06-10 | ||
PCT/EP1998/003428 WO1998056773A1 (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and its use as antiepileptic |
Publications (3)
Publication Number | Publication Date |
---|---|
HUP0002113A2 HUP0002113A2 (hu) | 2001-02-28 |
HUP0002113A3 HUP0002113A3 (en) | 2002-09-30 |
HU225153B1 true HU225153B1 (en) | 2006-07-28 |
Family
ID=4209650
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0002113A HU225153B1 (en) | 1997-06-10 | 1998-06-08 | Crystal modifications of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide, their use and pharmaceutical compositions containing them |
HU0000798A HU226107B1 (en) | 1997-06-10 | 1998-06-08 | New crystal modifications of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and pharmaceutical compositions containing them |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0000798A HU226107B1 (en) | 1997-06-10 | 1998-06-08 | New crystal modifications of 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide and pharmaceutical compositions containing them |
Country Status (37)
Country | Link |
---|---|
US (6) | US6740669B1 (zh) |
EP (2) | EP0994863B1 (zh) |
JP (2) | JP3672574B2 (zh) |
KR (2) | KR100425656B1 (zh) |
CN (3) | CN1298708C (zh) |
AR (4) | AR012946A1 (zh) |
AT (2) | ATE232852T1 (zh) |
AU (2) | AU725528B2 (zh) |
BR (2) | BR9804947A (zh) |
CA (3) | CA2256013C (zh) |
CO (2) | CO4940448A1 (zh) |
CY (1) | CY2007014I1 (zh) |
CZ (2) | CZ292481B6 (zh) |
DE (3) | DE122007000051I2 (zh) |
DK (2) | DK0994863T3 (zh) |
ES (2) | ES2192779T3 (zh) |
FR (1) | FR07C0037I2 (zh) |
HK (3) | HK1028242A1 (zh) |
HU (2) | HU225153B1 (zh) |
ID (2) | ID27660A (zh) |
IL (2) | IL125732A (zh) |
LU (1) | LU91345I2 (zh) |
MY (2) | MY120156A (zh) |
NL (1) | NL300284I2 (zh) |
NO (2) | NO329314B1 (zh) |
NZ (2) | NZ331370A (zh) |
PE (2) | PE79799A1 (zh) |
PL (2) | PL192114B1 (zh) |
PT (1) | PT994864E (zh) |
RU (2) | RU2198167C2 (zh) |
SI (2) | SI0994864T1 (zh) |
SK (2) | SK283734B6 (zh) |
TR (2) | TR199801631T1 (zh) |
TW (2) | TW526195B (zh) |
UY (1) | UY25844A1 (zh) |
WO (2) | WO1998056772A1 (zh) |
ZA (2) | ZA984967B (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW526195B (en) | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
DE60319980T2 (de) * | 2002-05-31 | 2009-04-16 | Schering Corporation | Xanthin-phosphodiesterase-v-hemmer polymorphe |
GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
US20090069390A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched rufinamide |
CA2736703A1 (en) | 2008-10-13 | 2010-04-22 | Cipla Limited | Process for the preparation of rufinamide |
CN101768124B (zh) * | 2008-12-30 | 2012-01-04 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
IT1395736B1 (it) * | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | Forme cristalline di rufinamide |
CN104817507A (zh) * | 2009-09-04 | 2015-08-05 | 巧妙疗法股份有限公司 | 用于制备5-氨基或取代的氨基1,2,3-三唑和三唑乳清酸盐制剂的新组合物和方法 |
EP2465853A1 (en) * | 2010-12-14 | 2012-06-20 | Laboratorios Lesvi, S.L. | Polymorph of rufinamide and process for obtaining it |
JP2013525413A (ja) * | 2010-04-30 | 2013-06-20 | ラボラトリオス レスヴィ,エス.エル. | ルフィナマイド中間体の改良された製造方法 |
ITMI20110718A1 (it) | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | Procedimento per la purificazione di rufinamide |
US10206874B2 (en) | 2012-07-20 | 2019-02-19 | Hetero Research Foundation | Rufinamide solid dispersion |
WO2021099481A1 (en) | 2019-11-20 | 2021-05-27 | Medichem, S.A. | Solid composition containing rufinamide |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3992378A (en) | 1973-12-26 | 1976-11-16 | Eli Lilly And Company | Fluoralkyl quinoxadinediones |
US4156734A (en) * | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
GB1511195A (en) | 1976-10-18 | 1978-05-17 | Ici America Inc | Triazole derivatives |
US4536518A (en) * | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
US4346097A (en) * | 1980-09-30 | 1982-08-24 | Warner-Lambert Company | Method for treating convulsions with pyrazole-4-carboxamide derivatives |
FI834666A (fi) | 1982-12-23 | 1984-06-24 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya aralkyltriazolfoereningar. |
US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
US4511572A (en) * | 1983-03-18 | 1985-04-16 | The University Of Kentucky Research Foundation | Triazoline anticonvulsant drugs |
PH22568A (en) | 1985-04-18 | 1988-10-17 | Ciba Geigy Ag | Fluorinated benzyl triazoles and pharmaceutical compositions containing the same |
CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
JPH02214504A (ja) | 1989-02-15 | 1990-08-27 | Nissan Chem Ind Ltd | 光学活性キノキサリン化合物の晶析法 |
EP0484437A4 (en) | 1989-07-27 | 1994-06-01 | Searle & Co | Renal-selective prodrugs for the treatment of hypertension |
IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
US5283244A (en) | 1990-11-06 | 1994-02-01 | Yamanouchi Pharmaceutical Co., Ltd. | Fused pyrazine derivatives |
JP2753911B2 (ja) | 1991-12-06 | 1998-05-20 | キッセイ薬品工業株式会社 | N−tert−ブチル−1−メチル−3,3−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 |
DE4217952A1 (de) | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
US5248699A (en) * | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
US5631373A (en) | 1993-11-05 | 1997-05-20 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
GB9419318D0 (en) | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
DK0812320T3 (da) | 1995-02-22 | 2003-04-14 | Aventis Pharma Ltd | Amorft piretanid, polymorfe former deraf, fremgangsmåde til fremstilling deraf og deres anvendelse |
SK283990B6 (sk) * | 1996-07-11 | 2004-07-07 | Novartis Ag | Spôsob prípravy 1-substituovaných 4-kyano-1,2,3-triazolov, 4-kyano-1-(2,6-difluórbenzyl)-1H-1,2,3-triazol |
TW526195B (en) * | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
-
1998
- 1998-06-04 TW TW087108858A patent/TW526195B/zh not_active IP Right Cessation
- 1998-06-04 TW TW087108859A patent/TW403740B/zh not_active IP Right Cessation
- 1998-06-08 IL IL12573298A patent/IL125732A/en not_active IP Right Cessation
- 1998-06-08 NZ NZ331370A patent/NZ331370A/xx not_active IP Right Cessation
- 1998-06-08 SI SI9830450T patent/SI0994864T1/xx unknown
- 1998-06-08 TR TR1998/01631T patent/TR199801631T1/xx unknown
- 1998-06-08 TR TR1998/01630T patent/TR199801630T1/xx unknown
- 1998-06-08 DE DE122007000051C patent/DE122007000051I2/de active Active
- 1998-06-08 PE PE1998000478A patent/PE79799A1/es not_active IP Right Cessation
- 1998-06-08 BR BR9804947A patent/BR9804947A/pt not_active Application Discontinuation
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 PL PL330798A patent/PL192114B1/pl unknown
- 1998-06-08 HU HU0002113A patent/HU225153B1/hu unknown
- 1998-06-08 DK DK98934929T patent/DK0994863T3/da active
- 1998-06-08 JP JP53628898A patent/JP3672574B2/ja not_active Expired - Lifetime
- 1998-06-08 DK DK98934930T patent/DK0994864T3/da active
- 1998-06-08 RU RU99104300/04A patent/RU2198167C2/ru active
- 1998-06-08 CA CA002256013A patent/CA2256013C/en not_active Expired - Lifetime
- 1998-06-08 PE PE1998000479A patent/PE80999A1/es not_active IP Right Cessation
- 1998-06-08 AU AU84371/98A patent/AU725528B2/en not_active Expired
- 1998-06-08 CN CNB2004100473675A patent/CN1298708C/zh not_active Expired - Lifetime
- 1998-06-08 JP JP53628998A patent/JP3672575B2/ja not_active Expired - Lifetime
- 1998-06-08 EP EP98934929A patent/EP0994863B1/en not_active Expired - Lifetime
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 US US09/125,329 patent/US6740669B1/en not_active Expired - Lifetime
- 1998-06-08 IL IL12573398A patent/IL125733A/en active Protection Beyond IP Right Term
- 1998-06-08 DE DE69813560T patent/DE69813560T2/de not_active Expired - Lifetime
- 1998-06-08 CZ CZ19982533A patent/CZ292481B6/cs not_active IP Right Cessation
- 1998-06-08 ES ES98934929T patent/ES2192779T3/es not_active Expired - Lifetime
- 1998-06-08 KR KR10-1998-0708150A patent/KR100425656B1/ko not_active IP Right Cessation
- 1998-06-08 SI SI9830405T patent/SI0994863T1/xx unknown
- 1998-06-08 ID IDW980065D patent/ID27660A/id unknown
- 1998-06-08 RU RU99104299/04A patent/RU2194041C2/ru active
- 1998-06-08 CA CA002256015A patent/CA2256015C/en not_active Expired - Lifetime
- 1998-06-08 AU AU84372/98A patent/AU725517B2/en not_active Expired
- 1998-06-08 BR BR9804946A patent/BR9804946A/pt not_active Application Discontinuation
- 1998-06-08 PT PT98934930T patent/PT994864E/pt unknown
- 1998-06-08 SK SK1094-98A patent/SK283734B6/sk not_active IP Right Cessation
- 1998-06-08 PL PL330764A patent/PL191943B1/pl unknown
- 1998-06-08 CN CNB988056755A patent/CN1159300C/zh not_active Expired - Lifetime
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1999
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2000
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2001
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2002
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2004
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2006
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